Assignment

Chapter 10: Haloalkanes and Haloarenes

1. Name the following halides according to IUPAC system:

(a) CH3CH(Br)CH=C(CH3)CH2Cl (b) C(CH3)2Br

(c) CH3CH(CH3)CH(Br)CH3 (d) ClCH2C=CCH2Br

(e) Cl----- (f) CH3CH ≡ CI

2. What happens when bromine attacks CH2=CH-CH2-C ≡ CH ?

3. Write the structures of the following organic compounds:

(i) 2-Chloro-3-methylpentane
(ii) 1-Chloro-4-ethylcyclohexane
(iii) 2-(2-Chlorophenyl)-1-iodo octane
(iv) 4-tert-Butyl-3-iodoheptane

4. Answer the following questions:

(i) What is meant by chirality of the compound? Give an example.
(ii) Which of the following compounds is more easily hydrolysed by KOH and why?
CH3CH(Cl)CH2CH3 or CH3CH2CH2Cl
(iii) Which one undergoes SN2 faster and why?
I Cl
Or

5. Which one of the following reacts faster in an SN1 reaction and why?
Cl
Cl or

6. State one use of DDT and iodoform. Why chloroform is kept in dark coloured bottles
completely filled?

7. What are ambident nucleophiles? Explain with the help of an example.

8. Write short notes on:

(a) Fittig reaction (b) Swartz reaction

9. Account for the following:

i) tert-Butyl chloride reacts with aqueous NaOH by SN1 mechanism while n-butyl chloride
reacts by SN2 mechanism.
ii) Among HI, HBr and HCl, HI is most reactive.
iii) Alkyl halides though polar, are immisible with water.
iv) Chlorobenzene is extremely less reactive towards nucleophillic substitution reaction.
10 Carry out the following conversions:
i) 1-Chlorobutane to n-octane
ii) Toluene to benzyl alcohol
iii) Benzyl chloride to benzyl alcohol

11. What will be the mechanism for the substitution of -Br by –OH in (CH3)2C(Br)CH2CH3?

12. Identify the following compounds from A to T:

acetone
(a) CH3CH2CH2Cl + NaI A A
heat

(b) (CH3)3CBr + KOH Ethanol, heat B

( c) CH3CH(Br)CH2CH3 + NaOH (aq) C

ethanol
(d) CH3CH2Br + KCN D

(e) (CH3)3CBr + H2O heat E

C2H5ONa, heat
(f) (CH3)2CHCH(Br)CH2CH3 F

(g) CH3CH2Cl + SbF3 heat G

(h) CH2=CHCH2Br + H2O H

(i) C6H4CH2Cl + C2H5ONa I
(j) CH3CH2CH2OH + SOCl2 J
peroxide
(k) CH3CH2CH=CH2 + HBr K
(l) CH3CH=C(CH3)2 + HBr L

(m) Br
+ CH3NH2 M

CH2Br

Cl2, FeCl3
(n) OH N

(o) CH2CH2OH
+ HBr O

(p) CH(CH3)2 + Br2 heat P